1-Azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-hydroxy-8-oxo-7-[(phenoxyacetyl)amino]-, (4-nitrophenyl)methyl ester, (6R,7S)-

Base Information

• Chemical Name: 1-Azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-hydroxy-8-oxo-7-[(phenoxyacetyl)amino]-, (4-nitrophenyl)methyl ester, (6R,7S)-
• CAS No.: 119892-46-5
• Molecular Formula: C23H21N3O8
• Molecular Weight: 467.435
• Mol file: 119892-46-5.mol

Synonyms:

Chemical Property of 1-Azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-hydroxy-8-oxo-7-[(phenoxyacetyl)amino]-, (4-nitrophenyl)methyl ester, (6R,7S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-hydroxy-8-oxo-7-[(phenoxyacetyl)amino]-, (4-nitrophenyl)methyl ester, (6R,7S)-

There total 19 articles about 1-Azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-hydroxy-8-oxo-7-[(phenoxyacetyl)amino]-, (4-nitrophenyl)methyl ester, (6R,7S)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

C29H26IN3O8 → p-nitrobenzyl 7β-[(phenoxyacetyl)amino]-3-hydroxy-1-carba-1-dethia-3-cephem-4-carboxylate (119892-46-5)

Guidance literature:

With dirhodium tetraacetate; In dichloromethane; for 0.2h;

DOI:10.1016/S0040-4039(97)01669-9

Reference yield: 72.0%

cis-α-diazo-β,4-dioxo-3-[(phenoxyacetyl)amino]-2-azetidinepentanoic acid, (4-nitrophenyl)methyl ester (119892-48-7) → p-nitrobenzyl 7β-[(phenoxyacetyl)amino]-3-hydroxy-1-carba-1-dethia-3-cephem-4-carboxylate (119892-46-5)

Guidance literature:

Rh₂(O₂CC₇H₁₅)4; In dichloromethane;

DOI:10.1016/S0040-4039(01)80388-9

Reference yield: 42.0%

[(3S,4R)-2-Oxo-3-(2-phenoxy-acetylamino)-4-(2-phenylsulfanylcarbonyl-ethyl)-azetidin-1-yl]-acetic acid 4-nitro-benzyl ester (131533-82-9) → p-nitrobenzyl 7β-[(phenoxyacetyl)amino]-3-hydroxy-1-carba-1-dethia-3-cephem-4-carboxylate (119892-46-5)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(00)97052-7

upstream raw materials:

[(3S,4R)-2-Oxo-3-(2-phenoxy-acetylamino)-4-(2-phenylsulfanylcarbonyl-ethyl)-azetidin-1-yl]-acetic acid 4-nitro-benzyl ester

cis-α-diazo-β,4-dioxo-3-[(phenoxyacetyl)amino]-2-azetidinepentanoic acid, (4-nitrophenyl)methyl ester

p-nitrobenzyl glyoxylate monohydrate

(3R-trans)-3-phenoxyacetylamino-4-phenylsulfonyl-2-azetidinone

Downstream raw materials:

p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylate

carbacephalosporin hydrochloride

(6R,7S)-3-Chloro-8-oxo-7-(2-phenoxy-acetylamino)-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester

7β-[(phenoxyacetyl)amino]-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylic acid